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181 South Road, Chilmark single family home — photo 1 of 35
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181 South Road

54Sleeps 10

Chilmark

$5,000 – $13,000 per week

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181 South Road

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Available year round

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!

The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.). It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach).

This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle. The house is fully air-conditioned and has Wi-Fi, high-speed Internet and cable TV.

A beautiful three-season porch was added to the back of the house. It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside. The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill. Adjacent to the patio is a large private outdoor shower.

The house is surrounded by an expansive lawn bordered by stonewalls.

The house is remarkably open on the first floor. The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops, and an island with seating. The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace.

The library/media room is a cozy place to sit and talk, read by the fireplace, or binge-watch that show you just never got to last year on a large flat-screen TV. The final room downstairs is the first, of two, en suite primary bedrooms (queen bed). It has a fireplace, flat-screen TV, and a marble and tile bathroom. A French door leads from this bedroom to the bluestone patio.

The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin, and an en suite king), a full laundry, and a large bathroom with an oversized tub/shower. The 2nd-floor primary bedroom (king bed) has a flat-screen TV, an attached walk-in closet, and an en suite marble and tile bath. High-quality linens and towels are provided throughout the house.

The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road. Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed.

Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket.

Beach chairs, towels, umbrellas, and coolers are all provided.

Wallace & Co. Sotheby’s International Realty attempts to accurately represent the Premises to the best of our ability. Our information is deemed reliable but not guaranteed. Opinions as to the condition of the Premises vary from individual to individual and are very subjective. We highly recommend that you personally view the property before signing the lease to verify the information in the advertised listing sheet. Be aware that numerous types of molds occur naturally on Martha’s Vineyard; some people may be sensitive to and have allergic reactions from the same. Any house built prior to 1978 may contain lead paint.

Bedrooms

Bedroom 1

Lower Level: Queen Bed, Private Bath, TV

Bedroom 2

Second Level: King Bed, Private Bath, TV

Bedroom 3

Second Level: Queen Bed, Shared Bath

Bedroom 4

Second Level: Queen Bed, Shared Bath

Bedroom 5

Second Level: Two Twin Beds, Shared Bath

Amenities

Featured Amenities

  • Beach - Association
  • Lawn / Garden Area
  • Outdoor Shower
  • AC - Central Air

Indoor Amenities

  • Den
  • Fireplace

General

  • Ceiling Fans
  • Hair Dryer
  • Iron/Ironing Board
  • Washer/Dryer
  • Vacuum

Linens

  • Linens - Provided
  • Beach Towels

Nearby Attractions

  • Beach - Town
  • Hiking Trails

Kitchen And Dining

  • Bakeware
  • Beverage Refrigerator
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Lobster Pot
  • Microwave
  • Oven/Stove
  • Pantry Items
  • Refrigerator
  • Toaster
  • Wine Fridge

Entertainment

  • Board Games
  • Wireless Internet
  • TV - Cable
  • TV - Smart TV

Outdoor Amenities

  • Beach Chairs
  • Beach Toys
  • Beach Umbrella
  • Cooler
  • Patio
  • Grill - Gas
  • Outdoor Dining Area
  • Outdoor Furniture

Request a booking

Not ready to pick dates? .

October 2026

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Rates & Availability

May 2027 – August 2027

May 2027

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$5,000/week
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$5,000/week
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$5,000/week
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$5,000/week
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$8,000/week

June 2027

Su
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$8,000/week
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$8,000/week
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$8,000/week
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$11,000/week

July 2027

Su
Mo
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$11,000/week
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$11,000/week
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$11,000/week
25
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$13,000/week

August 2027

Su
Mo
Tu
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$13,000/week
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$13,000/week
15
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$13,000/week
22
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$11,000/week
29
30
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$8,000/week
Available BookedCheck-out day — available from middayCheck-in day — available until the afternoon

Rates and availability are subject to change and may not be current. Published rates do not include local & state taxes. Please contact your Wallace & Co. Sotheby’s International Realty agent to confirm current rates and availability.

$5,000 – $13,000 per week

Request Information

Location

Chilmark

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